Orangutans and Character Design

Character design has always been a struggle for me.  When I was at BYU several years ago, I was so bad that I had to take Ryan Woodward's excellent character design class twice.  One assignment was to make characters based on animals, and the first time I tried an orangutan.  The result was so unappealing that I hate myself for having to post it:
I realize now that my problem wasn't my skill or lack thereof; it was a lack of knowledge, and more importantly, purpose.  All I did then was try to find a funny way to abstract the shapes that an orangutan was made out of, with maybe a little caricature.  What I needed to do instead to come up with a better design was have a more solid concept of who and what that character was supposed to be.  When you don't know anything about your character, it's hard to determine what kind of lines, shapes, proportions, or anything else to use to describe that character.  So what you end up with is a hodgepodge of decisions that don't lead the viewer toward any conclusions, which usually results in a less appealing character just because the chances of finding a great combination of elements at random aren't very high.
Armed with this knowledge, I decided to attack the problem again.  The lower left guy (image below) is where I started after doing some research on orangutans.  When I started to think about character types that fit with orangutans, my first thought was stereotypical surfers/hippies.  Then it hit me: Orangutans are the rednecks of the primate world.  So I did some more brainstorming and came up with a more specific personality/role that I liked for this orangutan.  My top drawings are starting to go somewhere.  If I was doing this character design for work I'd probably do about 20 more iterations to improve the idea and replace (where possible) stereotypical elements with more surprising ideas that filled the same purpose.  I already think the new guy (upper left) is a big improvement on the original, though.